A big contract is not always bad, and a small contract is not always good. The same can be said for long or short deals. Of course, most of the contracts on this list are both big and long, which naturally exposes the team to more risk, but failing to pony up can also leave a team vulnerable.
Many teams in baseball have simply decided not to sign players beyond a certain length or dollar figure, which may keep them off this list but has likely cost them the prime years of their home-grown stars (sorry, Royals fans).
There are plenty of bad deals to choose from, and this is just a selection of some of the worst. Feel free to comment with your own nominees.